KR960029366A - Copolyesters, molded articles produced therefrom, and aromatic triols - Google Patents

Copolyesters, molded articles produced therefrom, and aromatic triols Download PDF

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KR960029366A
KR960029366A KR1019960002266A KR19960002266A KR960029366A KR 960029366 A KR960029366 A KR 960029366A KR 1019960002266 A KR1019960002266 A KR 1019960002266A KR 19960002266 A KR19960002266 A KR 19960002266A KR 960029366 A KR960029366 A KR 960029366A
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triol
group
integer
independently
unit
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KR1019960002266A
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KR100196951B1 (en
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신지 다이
데쓰야 하라
아키라 가게유
쓰구노리 가시무라
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이즈미 마사노리
구라레 캄파니, 리미티드
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Priority claimed from JP07032803A external-priority patent/JP3095968B2/en
Priority claimed from JP1352395A external-priority patent/JP2851030B2/en
Priority claimed from JP07034710A external-priority patent/JP3095969B2/en
Application filed by 이즈미 마사노리, 구라레 캄파니, 리미티드 filed Critical 이즈미 마사노리
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66Polyesters containing oxygen in the form of ether groups
    • C08G63/668Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78Preparation processes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/13Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352Polymer or resin containing [i.e., natural or synthetic]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)

Abstract

A copolyester consisting essentially of ethylene terephthalate units and further comprising 0.01 to 1 mole % based on the sum of the moles of total diol units and the moles of triol units of a triol unit represented by the following formula (I) and/or a triol unit represented by the following formula (II). <CHEM> <CHEM> wherein A is a group represented by formula -CH2CH2- or formula -CH(CH3)CH2-, B is a divalent hydrocarbon group, -CO-, -SO2-, -O- or a direct bond (-), and p, q, r, s, t and u are each an integer of 1 to 8. A process for producing the same and molded articles (in particular extrusion blow molded articles) therefrom. The copolyesters of the present invention are applicable to melt moldings accompanying melt extrusion, in particular extrusion blow molding, where parisons therefrom have good draw-down tendency and blow moldability. The copolyesters can give, without causing troubles on molding, molded articles, in particular extrusion blow molded articles, having excellent transparency, heat resistance, moisture resistance and like properties. Aromatic triols usable for producing the above copolyesters are also provided.

Description

코폴리에스테르, 이로부터 제조된 성형품 및 이를 제조하는데 사용되는 방향족 트리올Copolyesters, molded articles produced therefrom, and aromatic triols

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (12)

필수적으로 에틸렌 글리콜 단위로 이루어진 디올 단위와 필수적으로 테레프탈산 단위로 이루어진 디카복실산 단위(i)를 포함하는 코폴리에스테르로서, 일반식(Ⅰ)의 트리올 단위(Ⅰ)(a)와 일반식(Ⅱ)의 트리올 단위(Ⅱ)(b)로 이루어진 그룹 중에서 선택된 하나 이상의 트리올 단위(ii)를, 전체 디올 단위(ii)의 트리올 단위의 mole의 합계를 기준으로 하여, 0.01 내지 1mole%의 양으로 추가로 포함하는 코폴리에스테르.A copolyester comprising a dicarboxylic acid unit (i) essentially consisting of a diol unit consisting of ethylene glycol units and essentially terephthalic acid units, wherein the triol unit (I) (a) of the general formula (I) ) Of at least one triol unit (ii) selected from the group consisting of triol units (II) (b), in an amount of 0.01 to 1 mole%, based on the total mole of triol units of the total diol units (ii) Copolyester further included as an amount. 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, 가 2가 탄화수소 그룹, 카보닐 그룹, 설포닐 그룹, 산소원자 또는 직접 결합(-)이며, p,q 및 r은 각각 독립적으로 1 내지 8의 정수이고, s, t 및 u는 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 - and is a divalent hydrocarbon group, a carbonyl group, a sulfonyl group, an oxygen atom or a direct bond (-), p, q and r are each independently an integer of 1 to 8, and s, t and u are each independently an integer of 1 to 8. 필수적으로 에틸렌 글리콜 단위로 이루어진 디올 단위와 필수적으로 테레프탈산 단위로 이루어진 디카복실산 단위(i)를 포함하는 코폴리에스테르로서, 일반식(Ⅲ)의 디올 단위(Ⅲ)(a)와 일반식(Ⅳ)의 디올 단위(Ⅳ)(b)로 이루어진 그룹 중에서 선택된 하나 이상의 디올 단위(ii), 일반식(Ⅰ)의 트리올 단위(Ⅰ)(a)와 일반식(Ⅱ)의 트리올 단위(Ⅱ)(b)로 이루어진 그룹 중에서 선택된 하나 이상의 트리올 단위(iii), 전체 디올 단위(iii)의 트리올 단위의 mole의 합계를 기준으로 하여, 1 내지 15mole%의 양으로 함유되는, 디올 단위(Ⅲ)와 디올 단위(Ⅳ)로 이루어진 그룹 중에서 선택된 하나 이상의 디올 단위(iv) 및 전체 디올 단위와 (iii)의 트리올 단위의 mole의 합계를 기준으로 하여, 0.01 내지 1mole%의 양으로 함유되는, 트리올 단위(Ⅰ)와 트리올 단위(Ⅱ)로 이루어진 그룹 중에서 선택된 하나 이상의 트리올 단위(Ⅴ)를 추가로 포함하는 코폴리에스테르.(III) and (IV) of the general formula (III), wherein the diol unit (III) is a copolyester comprising a dicarboxylic acid unit (i) essentially consisting of a diol unit consisting of ethylene glycol units and an essential terephthalic acid unit, (Ii) a triol unit (I) of the formula (I) and a triol unit (II) of the formula (II) (III), which is contained in an amount of 1 to 15 mole% based on the sum of the mole of the triol unit of the total diol unit (iii), the at least one triol unit (iii) selected from the group consisting of the diol units (Iv) selected from the group consisting of diol units (IV) and diol units (IV) and moles of triol units of the total diol units and (iii) in an amount of 0.01 to 1 mole% A group consisting of a triol unit (I) and a triol unit (II) Copolyester containing in the additional unit ol (Ⅴ) one or more selected the tree. 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, B는 2가 탄화수소 그룹, 카보닐 그룹, 설포닐 그룹, 산소원자 또는 직접 결합(-)이며, j 및 k는 각각 독립적으로 1 내지 8의 정수이고, m 및 n은 각각 독립적으로 1 내지 8의 정수이며, p, q 및 r은 각각 독립적으로 1 내지 8의 정수이고, s, t및 u는 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 -, B is a divalent hydrocarbon group, a carbonyl group, a sulfonyl group, an oxygen atom or a direct bond (-) , j and k are each independently an integer of 1 to 8, m and n are each independently an integer of 1 to 8, p, q and r are each independently an integer of 1 to 8, s, t and u Are each independently an integer of 1 to 8; 제1항 또는 제2항에 있어서, 고유점도가 0.6 내지 1.5dl/g인 코폴리에스테르.3. The copolyester according to claim 1 or 2, wherein the copolyester has an intrinsic viscosity of 0.6 to 1.5 dl / g. 제1항 또는 제3항에 있어서, 전단속도가 0.1rad/sec 및 온도 270℃에서의 용융점도(η1)가 5×104 내지 5×106poise이고, 전단속도 100rad/sec 및 온도 270℃에서의 용융점도(η2)가 조건 5×103내지 5×103poise이며, 용융점도(η1) 및 (η2)가 조건.The thermoplastic resin composition according to any one of claims 1 to 3, which has a melt viscosity (? 1 ) at a shear rate of 0.1 rad / sec and a temperature of 270 ° C of 5 x 10 4 to 5 x 10 poise, a shear rate of 100 rad / The melt viscosity (? 2 ) is in the condition of 5 × 10 3 to 5 × 10 3 poise, and the melt viscosity (η 1 ) and (η 2 ) are conditions. 0.7(1/3)log1021)-0.20.7 (1/3) log 10 (? 2 /? 1 ) -0.2 ①을 만족시키는 코폴리에스테르.Copolyester satisfying (1). 제2항 또는 제3항에 있어서, 전단속도가 0.1rad/sec 및 온도 (용점+40℃)에서의 용융점도(η3)가 5×104내지 5×106poise이고, 전단속도 100rad/sec 및 온도 (융점+40℃)에서의 용융점도(η4)가 조건 5×103내지 5×105poise이며, 용융점도(η3) 및 (η4)가 조건.The thermoplastic resin composition according to claim 2 or 3, which has a melt viscosity (? 3 ) of 5 × 10 4 to 5 × 10 6 poise at a shear rate of 0.1 rad / sec and a temperature (melting point + 40 ° C.) sec and a melt viscosity (? 4 ) at a temperature (melting point + 40 ° C) of 5 × 10 3 to 5 × 10 5 poise under conditions of melt viscosity (η 3 ) and (η 4 ). 0.7(1/3)log1043)-0.20.7 (1/3) log 10 (? 4 /? 3 ) -0.2 ②을 만족시키는 코폴리에스테르.Copolyester satisfying (2). 제1항 내지 제5항 중의 어느 한 항에 따르는 코폴리에스테르를 포함하는 성형품.A molded article comprising a copolyester according to any one of claims 1 to 5. 제6항에 있어서, 압출 취입 성형품인 성형품.The molded article according to claim 6, which is an extrusion blow-molded article. 제1항 내지 제5항 중의 어느 한 항에 따르는 코폴리에스테르를 압출 취입 성형시킴을 포함하는 성형품의 제조방법.A process for producing a molded article, comprising extrusion blow molding the copolyester according to any one of claims 1 to 5. 필수적으로 테레프탈산 또는 이의 에스테르 형성 유도체로 이루어진 디카복실산 성분(1), 필수적으로 에틸렌 글리콜로 이루어진 디올 성분(2) 및 일반식(Ⅴ)의 트리올(a)과 일반식(Ⅵ)의 트리올(b)로 이루어진 그룹 중에서 선택된 하나 이상의 트리올을, 전체 디올 성분과 (3)의 트리올 성분의 mole의 합계를 기준으로 하여, 0.01 내지 1mole%의 양으로 함유하는 트리올 성분(3)을 포함하는 출발물질을 에스테르화하거나 에스테르 교환 반응시키고, 수득된 반응 생성물을 용융 중측합시켜 폴리에스테르 예비중합체를 형성시킨 다음, 폴리에스테르, 예비중합체를 고상 중합시킴을 포함하여, 제1항 및 제3항 내지 제5항 중의 어느 한 항에 따르는 코폴리에스테르를 제조하는 방법.(1) consisting essentially of terephthalic acid or an ester-forming derivative thereof, a diol component (2) essentially consisting of ethylene glycol and a triol of the formula (V) and a triol of the formula (VI) (3) containing, in an amount of 0.01 to 1 mole%, at least one triol selected from the group consisting of the total diol component and the triol component (3) Comprising the steps of esterifying or transesterifying the starting materials of the polyester and the prepolymer, and subjecting the obtained reaction products to a mating reaction in the melt to form a polyester prepolymer, followed by solid phase polymerization of the polyester and the prepolymer. Lt; RTI ID = 0.0 &gt; 5, &lt; / RTI &gt; 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, B는 2가 탄화수소 그룹, 카보닐 그룹, 설포닐 그룹, 산소원자 또는 직접 결합(-)이며, p, q는 r은 각각 독립적으로 1 내지 8의 정수이고, s, t 및 u는 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 -, B is a divalent hydrocarbon group, a carbonyl group, a sulfonyl group, an oxygen atom or a direct bond (-) p, q and r are each independently an integer of 1 to 8, and s, t and u are each independently an integer of 1 to 8. 필수적으로 테레프탈산 또는 이의 에스테르 형성유도체로 이루어진 디카복실산 성분(1), 필수적으로 에틸렌 글리콜로 이루어지고, 일반식(Ⅶ)의 디올(a)과 일반식(Ⅷ)의 디올(b)로 이루어진 그룹 중에서 선택된 하나 이상의 디올을, 전체 디올 성분과 다음(3)의 트리올 성분의 mole의 합계를 기준으로 하여, 1 내지 15mole%의 양으로 함유하는 디올 성분(2) 및 일반식(Ⅴ)의 트리올(a)과 일반식(Ⅵ)의 트리올(b)로 이루어진 그룹중에서 선택된 하나 이상의 트리올을, 전체 디올 성분과 항목(3)의 트리올 성분의 mole의 합계를 기준으로 하여, 0.01 내지 1mole%의 양으로 함유하는 트리올 성분(3)을 포함하는 출발물질을 에스테르화하거나 에스테르 교환반응시키고, 수득된 반응 생성물을 용융 중측합시켜 폴리에스테르 예비중합체를 형성시킨 다음, 폴리에스테르, 예비중합체를 고상 중합시킴을 포함하여, 제2항 및 제5항 중의 어느 한 항에 따르는 코폴리에스테르를 제조하는 방법.A dicarboxylic acid component (1) essentially consisting of terephthalic acid or an ester-forming derivative thereof and a diol (b) consisting essentially of ethylene glycol and containing a diol (a) of the formula (VII) The diol component (2) containing the selected one or more diols in an amount of 1 to 15 mole% based on the total of the total diol component and the mole of the triol component in the following (3) and the triol of the general formula (V) , at least one triol selected from the group consisting of triols of the general formula (a) and the triol (b) of the general formula (VI) is added in an amount of 0.01 to 1 mole % Of the triol component (3) is subjected to an esterification reaction or an ester exchange reaction, and the resulting reaction product is subjected to the reaction during the melt-bonding to form a polyester prepolymer, and then a polyester, a prepolymerization A process for producing a copolyester according to any one of claims 2 to 5, including solid phase polymerization of the sieve. 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, B는 2가 탄화수소 그룹, 카보닐 그룹, 설포닐 그룹, 산소원자 또는 직접 결합(-)이며, j 및 k는 각각 독립적으로 1 내지 8의 정수이고, m 및 n는 각각 독립적으로 1 내지 8의 정수이며, q,p 및 r은 각각 독립적으로 1 내지 8의 정수이고, s, t 및 u는 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 -, B is a divalent hydrocarbon group, a carbonyl group, a sulfonyl group, an oxygen atom or a direct bond (-) , j and k are each independently an integer of 1 to 8, m and n are each independently an integer of 1 to 8, q, p and r are each independently an integer of 1 to 8, s, t and u Are each independently an integer of 1 to 8; 하기 일반식(Ⅴ)의 방향족 트리올.An aromatic triol of the general formula (V) 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, B는 2가 탄화수소 그룹, 카보닐 그룹, 설포닐 그룹, 산소원자 또는 직접 결합(-)이며, p, q는 r은 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 -, B is a divalent hydrocarbon group, a carbonyl group, a sulfonyl group, an oxygen atom or a direct bond (-) , p, q, and r each independently represent an integer of 1 to 8. 하기 일반식(Ⅵ)의 방향족 화합물.An aromatic compound of the general formula (VI) 상기 식에서, A는 구조식 -CH2CH2- 또는 -CH(CH3)CH2-의 그룹이고, s, t 및 u는 각각 독립적으로 1 내지 8의 정수이다.Wherein A is a group of the structure -CH 2 CH 2 - or -CH (CH 3 ) CH 2 -, s, t and u are each independently an integer of 1 to 8. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960002266A 1995-01-31 1996-01-31 Copolyesters, molded articles from the same and method for producing the same KR100196951B1 (en)

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